N,N'-(5-cyano-3a,7a-dihydro-1H-pyrazolo[3,4-b]pyridine-3,6-diyl)diacetamide | 1184935-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: N,N'-(5-cyano-3a,7a-dihydro-1H-pyrazolo[3,4-b]pyridine-3,6-diyl)diacetamide
• 英文别名: N,N''-(5-cyano-1H-pyrazolo[3,4-b]pyridine-3,6-diyl)diacetamide；N-(3-acetamido-5-cyano-1H-pyrazolo[3,4-b]pyridin-6-yl)acetamide
• CAS: 1184935-19-0
• 化学式: C₁₁H₁₀N₆O₂
• 分子量: 258.239
• InChiKey: KMBXPOZIEPKWDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酸酐 、 3,6-Diamino-5-cyan-1H-pyrazolo<3,4-b>pyridin 反应 21.0h， 以8%的产率得到N,N'-(5-cyano-3a,7a-dihydro-1H-pyrazolo[3,4-b]pyridine-3,6-diyl)diacetamide
  参考文献：
  名称：

  Studies on the acetylation of 3,6-diamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile derivatives

  摘要：

  Abstract magnified image The acetylation reaction of the differently substituted 3,6‐diamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile derivatives 1, 2, 3, 4, 5, 6 is reported. The structure of the resulting acetamides has been investigated and confirmed by analytical, spectroscopic, and chemical transformations. From these studies, we conclude that, in general, under mild conditions, and using acetic anhydride, when free, the N(1)H moiety is a more reactive center respect to the C(3)NH2 and C(6)NH2 groups. This trend is reversed when no steric hindrance due to presence of a phenyl group at C4 drives the preferred acetylation to C(3)NH2, as it is evident by comparing the observed results from precursor 1 with 3. When N1 is blocked, the (C3)NH2 group undergoes preferential acetylation over the (C6)NH2 site, which only has been mono (or diacetylated) at reflux. Computational analyses based on DFT studies have been extensively used to explain the observed reactivities. J. Heterocyclic Chem., (2010).

  DOI：

  10.1002/jhet.403

文献信息

• Studies on the acetylation of 3,6-diamino-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile derivatives
  作者：Mourad Chioua、Elena Soriano、Abdelouahid Samadi、J. Marco-Contelles

  DOI：10.1002/jhet.403

  日期：——

  Abstract magnified image The acetylation reaction of the differently substituted 3,6‐diamino‐1H‐pyrazolo[3,4‐b]pyridine‐5‐carbonitrile derivatives 1, 2, 3, 4, 5, 6 is reported. The structure of the resulting acetamides has been investigated and confirmed by analytical, spectroscopic, and chemical transformations. From these studies, we conclude that, in general, under mild conditions, and using acetic anhydride, when free, the N(1)H moiety is a more reactive center respect to the C(3)NH2 and C(6)NH2 groups. This trend is reversed when no steric hindrance due to presence of a phenyl group at C4 drives the preferred acetylation to C(3)NH2, as it is evident by comparing the observed results from precursor 1 with 3. When N1 is blocked, the (C3)NH2 group undergoes preferential acetylation over the (C6)NH2 site, which only has been mono (or diacetylated) at reflux. Computational analyses based on DFT studies have been extensively used to explain the observed reactivities. J. Heterocyclic Chem., (2010).